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Method for synthesizing piperlongumine compounds

A technology of Piperamide and synthesis method, which is applied in the field of synthesis of alkaloid compounds, can solve the problems of time-consuming plant extraction, compound separation, laborious input-output ratio, etc., and achieves low raw material prices, mild reaction conditions, and easy operation methods. easy effect

Inactive Publication Date: 2010-07-14
BEIJING OKEANOS TECH
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AI Technical Summary

Problems solved by technology

These plant extracts often contain a variety of chemical components such as: piplartine (piperlongumine), dihydropiperlongumine (dihydropiperlonguminine), piperine (pipercide), palmitic acid (palmitic acid), tetrahydropiperic acid (tetrahydro-piperic acid), piperine, sesamin, guineensine, N-isobutyloctadeca-2,4-dienamide (N-isobutyloctadeca-2(E ), 4(E)-dienamide), N-isobutyleicosa-2,4-dienamide (N-isobutyleicosa-2(E)-4(E)-dienamide), etc. These chemical compositions have similar Physicochemical properties often cause difficulties such as compound separation and low production efficiency
Moreover, the large-scale production of plant extraction will also cause certain environmental problems.
[0007] This shows that plant extraction method is time-consuming, laborious and low in input-output ratio, therefore, the chemical synthesis method of development Piperamides compound just has important significance

Method used

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  • Method for synthesizing piperlongumine compounds
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  • Method for synthesizing piperlongumine compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 aromatic carboxylic acid:

[0028]

[0029] Reagents and conditions: a) propionic acid, pyridine, piperidine; b) H 2 , Pd / C, ethanol.

[0030] 3,4,5,-Synthesis of trimethoxycinnamic acid: 3,4,5,-trimethoxybenzaldehyde 39.2g (0.2mol) and malonic acid 41.6g (0.4mol), dissolved in 300ml pyridine, And add 2.5ml of piperidine, heat to 50°C, react for 3h, until the raw materials are completely reacted, cool to room temperature, add 2M hydrochloric acid to adjust the solution to pH=5, extract with ethyl acetate (200ml×3), combine the organic phases, and separate Washed with saturated brine and secondary water, anhydrous Na 2 SO 4 Dry, concentrate to get crude product, crude product with CH 3 OH·H 2 O was recrystallized to obtain 34.7 g of colorless needle crystals, with a yield of 72%.

[0031] 1 H-NMR: (400MHz, CDCl 3 , ppm) δ: 3.93 (s, 9H), 6.37 (d, 1H), 6.82 (s, 2H), 7.79 (d, 1H), .11.3 (b, 1H) MS-ESI (m / z): 239 (M+H) + .

[0032]...

Embodiment 2

[0034] The synthesis of embodiment 2 amino compounds:

[0035]

[0036] Synthesis of 5,6-dihydro-2(1)-pyridone: 20g vinyl acrylic acid ((E)-penta-2,4-dienoic acid) (0.051mol) and 100ml ammonia water (0°C saturated) were placed in In a 500ml autoclave, heat to 180°C, react for 24h, cool to room temperature, concentrate the reaction solution to obtain a syrupy viscous liquid, add hot methanol, and reflux for 3h, cool to room temperature, concentrate, remove the reaction solvent methanol, reduce Pressure distillation, collection 120 ~ 125 ℃ / 1mmHg, to obtain the product 6g. The target compound is unstable, so it is best to use it now.

[0037] 1 H-NMR: (400MHz, CDCl 3 , ppm) δ: 2.31 (m, 2H), 3.43 (t, 2H), 6.23 (m, 2H), .7.8 (b, 1H, NH), MS-EI (m / z): 97 (M) + .

[0038] The synthesis of 6-methyl-5,6-dihydro-2(1)-pyridone: 20g sorbic acid (2E, 4E)-hexa-2,4-dienoic acid (0.051mol) and 100ml ammonia water (0 ℃ saturated) in a 500ml autoclave, heated to 180°C, reacted for 24...

Embodiment 3

[0040] The synthesis of embodiment 3 Piperamide (compound 1):

[0041]

[0042] 3,4,5-trimethoxycinnamic acid (0.714g, 3mmol) was dissolved in 25ml of dry dichloromethane, 5,6-dihydro-2(1)-pyridone (0.35g, 3.6mmol) was added, and the reaction The system was cooled to -20°C, DCC (0.68 g, 3.3 mmol) was added, the reaction system was gradually warmed to room temperature, and the reaction was continued overnight.

[0043] After the reaction is complete, the reaction system is respectively washed with saturated NaHCO 3 The solution was washed with water twice, the organic phase was dried with magnesium sulfate, concentrated, and the crude product was separated on a silica gel column (eluent: petroleum ether / ethyl acetate=1 / 1) to obtain 0.6 g of Piperamide, yield: 63%.

[0044] 1 H-NMR: (400MHz, CDCl 3 , ppm) δ: 2.45(m, 2H), 3.92(s, 9H), 4.05(m, 2H), 6.12(m, 1H), 6.80(s, 2H), 6.94(m, 1H), 7.37(m , 1H), 7.75 (m, 1H). MS-EI (m / z): 317 (M) + .

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Abstract

The invention provides a method for synthesizing piperlongumine compounds, wherein the compounds are coupled by adopting acromatic carboxylic acid and amido compounds in the presence of coupling reagent. The method has the advantages of mild reaction condition and simple and convenient operation method, and is suitable for batch production of the compounds.

Description

technical field [0001] The present invention relates to a kind of synthetic method of alkaloid compound, in particular, relate to a kind of synthetic method of Piperamide compound. Background technique [0002] Piperamide, also known as Piperlongumine, Piplartine, the English name is piperlongumine or piplartine, and its chemical formula is: C 17 h 19 NO 5 , the molecular weight is 317.34, and the CAS number is 20069-09-4. [0003] Piperamide is an alkaloid compound, which is a white flashing needle crystal (ethanol-ether), with a melting point of 124°C. It mainly comes from the fruits, roots and stems of Piper longum L., a plant of the family Piperaceae. [0004] As a traditional Chinese herbal medicine, Piperumba has been widely used in my country since ancient times. Traditional Chinese medicine believes that it is hot in nature, pungent in taste, and returns to the stomach and large intestine meridians. According to the "Chinese Pharmacopoeia" records: it has the ef...

Claims

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Application Information

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IPC IPC(8): C07B43/06C07D211/86C07D211/70C07D295/192
Inventor 余明辉高源
Owner BEIJING OKEANOS TECH
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